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Molecules 2005, 10(1), 217-225; doi:10.3390/10010217
Article

Application of [Hydroxy(tosyloxy)iodo]benzene in the Wittig-Ring Expansion Sequence for the Synthesis of β-Benzocyclo-alkenones from α-Benzocycloalkenones

 and *
Department of Chemistry, The University of Akron, USA
* Author to whom correspondence should be addressed.
Received: 5 July 2004 / Accepted: 14 July 2004 / Published: 31 January 2005
(This article belongs to the Special Issue Hypervalent Iodine)
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Abstract

The conversion of α-benzocycloalkenones to homologous β-benzocyclo-alkenones containing six, seven and eight-membered rings is reported. This wasaccomplished via a Wittig olefination-oxidative rearrangement sequence using[hydroxy(tosyloxy)iodo]-benzene (HTIB) is the oxidant, that enables the synthesis ofregioisomeric pairs of methyl-substituted β-benzocycloalkenones. The incorporation ofcarbon-13 at C-1 of the β-tetralone nucleus was also demonstrated. The Wittig-HTIBapproach is a useful alternative to analogous sequences in which Tl(NO3)3·3H2O or thePrevost combination (AgNO3/I2) are employed in the oxidation step.
Keywords: [Hydroxy(tosyloxy)iodo]benzene; benzocycloalkenones; ring expansion; oxidative rearrangement [Hydroxy(tosyloxy)iodo]benzene; benzocycloalkenones; ring expansion; oxidative rearrangement
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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Justik, M.; Koser, G. Application of [Hydroxy(tosyloxy)iodo]benzene in the Wittig-Ring Expansion Sequence for the Synthesis of β-Benzocyclo-alkenones from α-Benzocycloalkenones. Molecules 2005, 10, 217-225.

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